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Unravelling a New Class of Chiral Organocatalyst for Asymmetric Ring-Opening Reaction of Meso Epoxides with Anilines

Manish Kumar, Rukhsana I. Kureshy*, S. Saravanan, Shailesh Verma, Ajay Jakhar, Noor-ul H. Khan, Sayed H. R. Abdi and Hari C. Bajaj

*Central Salt and Marine Chemicals Research Institute (CSMCRI), Council of Scientific & Industrial Research (CSIR), G. B. Marg, Bhavnagar 364 002 Gujarat, India, Email: rukhsana93yahoo.co.in

M. Kumar, R. I. Kureshy, S. Saravanan, S. Verma, A. Jakhar, N.-u. H. Khan, S. H. R. Abdi, H. C. Bajaj, Org. Lett., 2014, 16, 2798-2801.

DOI: 10.1021/ol500699c (free Supporting Information)


Abstract

A readily synthesized chiral sulfinamide based organocatalyst enables an asymmetric ring-opening (ARO) reaction of meso epoxides with anilines in high yields of with excellent enantioselectivity at room temperature. A probable mechanism for the catalytic ARO reaction is envisaged by 1H and 13C NMR experiments.

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Key Words

β-amino alcohols, organocatalysis


ID: J54-Y2014